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Sterically hindered 3-pyridinols Communication 5. Study of the course of aminomethylation and hydroxymethylation reactions in the 2-alkyl-3-pyridinol series with the aid of proton magnetic resonance and of chemical methods

  • L. D. Smirnov
  • V. P. Lezina
  • V. F. Bystrov
  • K. M. Dyumaev
Organic and Biological Chemistry
  • 21 Downloads

Summary

  1. 1.

    The course of aminomethylation and hydroxymethylation in the 2-alkyl-3-pyridinol series was studied with the aid of proton magnetic resonance and chemical methods.

     
  2. 2.

    Methods were developed for the synthesis of 6-(aminomethyl)-[6-(hydroxymethyl)-] and 4,6-bis(dialkylammo)-2-methyl-3-pyridinols.

     
  3. 3.

    The 6-mono(aminomethyl) derivative is formed at first, and this reacts further in the 4-position of the pyridine ring with formation of the 4,6-bis(dialkylaminomethyl) derivative.

     
  4. 4.

    5-Hydroxy-6-methyl-2,4-pyridinedimethanol (isopyridoxine) was synthesized.

     

Keywords

Proton Magnetic Resonance Pyridine Chemical Method Hydroxymethyl Pyridine Ring 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Literature cited

  1. 1.
    K. M. Dyumaev, L. D. Smirnov, and V. F. Bystrov, Izv. AN SSSR, Otd. Khim. N., 883 (1962).Google Scholar
  2. 2.
    L. D. Smirnov, V. P. Lezina, V. F. Bystrov, and K. M. Dyumaev, Izv. AN SSSR, Otd. Khim., N. 752 (1963).Google Scholar
  3. 3.
    L. D. Smirnov, S. I. Sholina, K. E. Kruglyakova, and K. M. Dyumaev, Izv. AN SSSR, Otd. Khim. N., 890 (1963).Google Scholar
  4. 4.
    L. D. Smirnov, K. M. Dyumaev, N. I. Shuikin, and I. F. Bel'skii, Izv. AN SSSR, Otd. Khim. N., 2246 (1962).Google Scholar
  5. 5.
    E. B. Burlakova, V. D. Gaintseva, L. V. Slepukhina, N. G. Khrapova, and N. M. ÉmanuÉl', Dokl. AN SSSR,155, 1398 (1964).Google Scholar
  6. 6.
    Preobrazhenskii and É. I. Genkin, Chemistry of Organic Medicinals [in Russian], Goskhimizdat, Moscow-Leningrad (1953).Google Scholar
  7. 7.
    T. Urbanski, J. Chem. Soc., 1104 (1946).Google Scholar
  8. 8.
    A. Stempel and E. C. Buzzi, J. Amer. Chem. Soc.,71, 2969 (1949); R. F. Brown and S. I. Miller, J. Organ. Chem.,11, 388 (1946).Google Scholar
  9. 9.
    L. A. Perez-Medina, R. P. Mariella, and S. M. McElvain, J. Amer. Chem. Soc.,69, 2574 (1947).Google Scholar
  10. 10.
    Organic Reactions,1 [Russian translation], IL, Moscow (1948), p. 403.Google Scholar
  11. 11.
    L. M. Jackmann, Application of NMR Spectroscopy in Organic Chemistry, Pergamon Press, London (1959); J. A. Pople, W. G. Schneider, and H. J. Bernstein, High-Resolution Nuclear Magnetic Resonance [Russian translation], IL, Moscow (1962).Google Scholar
  12. 12.
    V. F. Bystrov, K. M. Dyumaev, V. P. Lezina, and G. A. Nikiforov, Dokl. AN SSSR,148, 1077 (1963).Google Scholar
  13. 13.
    V. A. Afanas'ev, V. F. Bystrov, L. L. Dekabrun, Yu. N. Kil'yanov, and A. U. Stepanyants, Zavodsk. laborat., No. 1, 102 (1962).Google Scholar

Copyright information

© Consultants Bureau 1966

Authors and Affiliations

  • L. D. Smirnov
    • 1
  • V. P. Lezina
    • 1
  • V. F. Bystrov
    • 1
  • K. M. Dyumaev
    • 1
  1. 1.Institute of Chemical PhysicsAcademy of SciencesUSSR

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